


Watch Over You

by fiveyaaas



Category: The Umbrella Academy (TV)
Genre: Daddy Kink, F/M, Five is watching while he’s in the commission, Guilt, Masturbation, Mutual Masturbation, Older Man/Younger Woman, Plot What Plot/Porn Without Plot, Sex Work, Sugar Daddy, Vaginal Fingering, Vanya is a cam girl, i apologize for all inaccuracies to cam work, mildly, this is so gross I’m sorry, vanya is not mad at five for this just to clarify it’s all consensual
Language: English
Status: Completed
Published: 2020-08-13
Updated: 2020-08-13
Packaged: 2021-03-06 01:33:27
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,979
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25885138
Author URL: https://archiveofourown.org/users/fiveyaaas/pseuds/fiveyaaas
Summary: Five keeps tabs on his family during his time in the Commission. What he finds shocks him.
Relationships: Number Five | The Boy/Vanya Hargreeves
Comments: 25
Kudos: 226





	Watch Over You

**Author's Note:**

  * For [sweetheartbitterheart](https://archiveofourown.org/users/sweetheartbitterheart/gifts).



> Hello!!! Thank you so much to the discord people for listening to me talk about this, and for sweetheartbitterheart for giving the original prompt!!! 
> 
> First of all, I know nothing about cam work and I hope I didn’t make this seem disrespectful at all. Any inaccuracies I apologize for. 
> 
> Second of all, all of this is 100% consensual on both ends!! Five feels guilty for not telling Vanya who he is, but this is not dub-con and Vanya is encouraging of all of these interactions. 
> 
> Okay, now all that being said, I’m sorry this is gross lmao.

Despite the fact that he had become an assassin for the Commission, Five’s family never once left his mind. Once he worked for the Commission, he actually had access to seeing how his family was doing. He had done a lot of research into how exactly he could bring Ben back and keep him from dying like Vanya’s book reported he would, but until he was certain he knew how, he would not risk it. Plus, he noted grimly, he couldn’t visit them until the Handler was certain that he was a loyal little soldier. 

He thought frequently of how exactly he wanted to kill the Handler. 

She had not found out about him keeping tabs on his family, or else he knew that he would have heard about it. 

Luther was still following Reginald around like the good soldier Five was pretending to be for the Commission. His behavior was so predictable that it did not take Five long at all to find information on him. Allison was also relatively easy to keep up with, all kinds of celebrity news columns talking about her. Neither of them brought much concern to Five’s mind. He knew Luther could handle his own, and he knew if he thought about his brother being hurt too long, it would hurt him anyways. 

Diego and Klaus were a little harder to keep tabs on. Diego, being a vigilante type, tried to live in as much obscurity as someone throwing knives at criminals could muster. Klaus’s life was the opposite of subtle, but he checked into rehabs under all kinds of names, lived in partners’ houses for days or weeks before eventually leaving, and spent a lot of time on the streets. 

It was actually when Five was finding ways to send money to Klaus so he wouldn’t starve or die in an alley somewhere that he even found Vanya. Five had searched for her first, had searched for her the most, but many of the records on Vanya were blocked out and impossible to access. Whatever the Commission planned for her (and he would inevitably have to stop, he reminded himself, already willing to do whatever it took to keep her safe), it was something that they didn’t want any of the corrections division knowing about ( _ especially  _ Five, he imagined.) 

Five had found her by complete accident, searching through a website that he had found in Klaus’s file. He figured of all of them Klaus would be the one to be doing cam porn, but he found out also that he would be able to wire money to Klaus this way (and, no, he wasn’t going to watch the videos of Klaus, Klaus would probably like that way too much.) It was as he was searching for Klaus that he saw a familiar shade of hair and he snapped his gaze back to the screen, already hating himself for clicking on the link. 

_ It’s not Vanya, _ he quickly told himself. The woman didn’t even have her face shown in the picture. 

Of course, as one would assume, he was proven wrong the second the screen zoomed in and went to the woman’s page. His eyes landed on a specific scar on her knee and the birthmark on her hip, and he knew. 

Her voice was shaky as it let out whines brought on by the trembling hand holding a small toy. 

Five’s first reaction, and he silently thanked the universe for not completely depriving the last shred of goodness inside of him, was to be concerned. Vanya was clearly in a rough position to be doing this. She wouldn’t  _ do  _ this, expose herself, unless it was a last resort. Without even thinking about it, he wires over what would probably be considered an  _ exorbitant  _ amount for someone watching a cam video. He just had to make sure that she wouldn’t struggle with rent (or by the looks of how thin she was, food either), and when he gave the money a message popped up asking if he was fine with the person receiving the money to message him. He almost clicked “no” but then he thought of the slim chance of Vanya being able to communicate with him, and he shamefully clicked “yes.”

He turned the screen off of Vanya, not wanting to see any more of that with how much guilt was churning in his stomach. He glanced down at the pants of the suit he was wearing, sickened with how he had reacted to seeing her spread out and moaning. The way she dipped the toy-

_ Fuck _ . He was an awful person. Truly awful. She was struggling, and he was thinking of  _ that _ . Her breathy moans, her shaking thighs-

He needed a drink. 

***

Five would have never looked at her again, he was pretty certain, but he got a notification of her messaging him and he decided to abandon that shred of morality for just the length of the time to read the message. 

“ _ Oh my goodness, thank you so much for giving that much, that was so sweet! _ ”

Five frowned at what Vanya had written. She thought it was  _ sweet  _ that some perv gave her that much money? Wasn’t she worried about him being a stalker with nefarious plans? Was she not raised in the same home as him?

He couldn’t exactly say, “What if I was a murderer, Vanya?” He furrowed his brow, typing out a quick reply. 

“ _ It was nothing. You’re welcome. _ ”

“ _ Do you have any specific requests for future streaming? _ ”

Five wasn’t sure if he choked on his coffee or if it sprayed onto the monitor, perhaps a bit of both. 

Then, he frowned. Hadn’t he given her enough that she wouldn’t need to do this any longer?

“ _ Was what I gave not enough? I could give you more if you need.” _

Vanya responded quickly. 

“ _ Oh, no, I’m so sorry for making it seem like I assumed I wanted more!!! I was just trying to say thank you, but looking back on it maybe I sent that wrong? _ ”

Five wanted to plant his head on the keyboard. Vanya was  _ apologizing  _ to him for his intrusion of her privacy. He was tempted to wire her more, enough that she would certainly be okay until he could safely come back to her, and just close the chat and forget he had ever seen this. His mind flashed to the fear in her eyes before he time travelled, to the sadness in the smile on the back cover of her book. 

He couldn’t  _ not  _ talk to her when he had the opportunity. Yes, it made him wrong. He  _ knew,  _ and he hated it, but he couldn’t take this one comfort away. 

“ _ Absolutely no worries! If you ever do want more, though, just ask. I understand that it can be a struggle to pay bills and whatnot. I can’t imagine you’d do this any other way.” _

Shit. He could have blown his cover there, couldn’t he? Fuck, fuck,  _ fuck.  _

“Please don’t hate me,” he whispered out loud, knowing no one would hear him and feeling emboldened by the fact. 

“ _ Oh, no, am I that obvious? Yeah, I know it’s cliche, but this really is about paying the rent. The student loans are bad too, to worsen the cliche. _ ”

Startled, he felt himself laugh before typing quickly. 

“ _ If you ever need more help, just tell me. _ ”

He almost closed the chat before her response came though. 

“ _ I don’t feel comfortable asking for more unless I’m actually doing something for you in particular, so please do tell me what you want to see! _ ”

He wanted to see her face after a long mission when she would climb into his bed and say it was because of a nightmare (when they both knew that on the nights of his missions, it was about making sure she felt secure he really was home, and that he felt secure in that she would be safe from whatever dangers he had faced earlier next to him.) He wanted to see her chiding him gently as she wrapped up a wound he had gotten, saying that he needed to be more careful. He wanted to see the smile she gave him when he said that she was his favorite. 

“ _ I want to see you in a skirt and knee high socks when you touch yourself. _ ”

Apparently he had abandoned his morality longer than he had intended. 

***

Five was still cleaning the blood off of himself from his mission when he watched the live video she had posted specifically for him. She didn’t really say anything, but he knew that it was meant for him with what she was wearing in it. His eyes flicked over her form in the grainy camera. 

He should feel bad, right? If Vanya knew who was paying her, she would be upset, right?

He couldn’t do this. He couldn’t. 

She gasped, and he realized she was just using her hands this time. She wasn’t wearing the academy uniform, but the effect was still the same on him. 

He wished he was there with her. 

His hands slipped into his pants, and he settled for hearing her mouth whimper unintelligible noises instead. 

***

She started performing videos that were clearly meant for him, doing whatever he asked. He didn’t try at first to ask for anything too out of the ordinary. He kept giving her money, and she kept performing for him. 

When she spoke to him in her messages, it was pretty non-sexual. It was actually just like they were chatting. She often asked about his life, if he was okay. He realized once when his hand was working furiously against his cock that even though she was essentially fucking herself only for his eyes at this point, she was treating it with the sweetness of the Vanya he had always known. He had come shamefully at the thought, not sure how much tenderness should really play into jerking off. 

***

“ _ What is your name? _ ”

Five frowned at Vanya’s message. He wondered idly if she would figure out who he was if he just said “I don’t have one,” something that technically could be true. He had a number, not a name though. 

“ _ Why do you ask? _ ”

He wondered if she had that soft smile she got when he was being particularly difficult. 

“ _ I want to know what to call out when I fuck myself to you. _ ”

Five coughed, face somehow aflame. Maybe there was some sort of fire or something around and that’s what was wrong because he was  _ not  _ blushing like he was the same twelve year old who turned bright red when Vanya had kissed his cheek for giving her a birthday present.

“ _ Why do you have to call me something, sweetheart? _ ”

This was actually not the first time he had used a pet name in these chats. She didn’t seem to mind, seeming to actually encourage it if anything. Five probably should be more concerned by how Vanya seemed just as enthusiastic about this as him. How  _ lonely _ did she have to be to be to be treating these interactions with so much excitement? He hoped it was just money for her, that way she wasn’t really so starved of affection that she would catch feelings for someone she had assumed to have never met. 

“ _ Wouldn’t it be better for you too? _ ”

She said “too.” Implying she wanted to call him something. It was for her just as much as it was for him. 

He couldn’t tell her though. One, he was ashamed. Two, it was not like he could  _ go _ to her, and be with her. It would get her hopes up. 

He suddenly wanted her to push him away. Wanted her to be disgusted with him as he was of himself. He said the darkest thing he could imagine saying, hoping to drive her away.

“ _ Call me Daddy if you want to call me anything. _ ”

Good. She would hate him, and he could sober himself from what was becoming a much stronger addiction than any other of the substances he consumed. 

“ _ Okay, Daddy. _ ”

Fuck. 

***

Five wanted more than anything to see Vanya’s face as she fucked herself, but he never asked her of that because she was clearly only showing her neck and down for a reason- her comfort. He couldn’t really give her much, and he wouldn’t violate that. 

He still would love to see the way her lips shaped over the dirty name he had asked her to call him though.

He never asked, but he wanted to see it. Actually, he wanted to hear her say “Five” while she was settled into his lap and he could actually touch her, but then again beggars couldn’t be choosers. 

Vanya inadvertently gave him some of his wish though, and he considered for a brief instance leaving the Commission right in that moment and going to her when she accidentally said “Five.”

He didn’t ask her about it, and she didn’t mention it. But as he jerked off later, he thought of the breathless way she had said his name over and over until he came against his hand. 

At least Vanya wanted things she couldn’t have too.

***

She made a point to say “Daddy” frantically now, like she was trying to replace Five’s name on her lips. She didn’t want to make the mistake again, and she doubled down on whimpering “Daddy.” 

She didn’t know she was calling out for the same person. 

***

The Handler found out about his vice later than he expected. Also, in the worst possible way. 

She had flicked her gaze against his still hard dick, smirking at him. And then she saw the video playing and there was anger for a flash that he imagined he only caught because he was trained in observational skills. She schooled her features into cool condescension, quirking her lips up at him in what was forced to be too kind to be a sneer. 

“Missing your little sister, Number Five?” 

She said it because she  _ knew  _ he would be ashamed. But Five had already gotten over most of the shame, clinging onto his Vanya long enough that he wouldn’t let her see any of the shame that lingered. 

“Well, she was always my favorite,” Five commented. He could hear Vanya whimpering in the background, frantic as she was near coming. He wondered what the Handler thought of hearing Vanya yelling “Daddy” while she fucked herself. It was pretty common knowledge they all had daddy issues, at least.

“You’re aware that until you retire your loyalties lie with the Commission, right?” the Handler asked with a disappointed cluck of her tongue. 

“I don’t see how jerking off takes away my ability to murder for you, personally.”

“Your little obsession with the girl will not be tolerated. Until you are done here, you are loyal here.”

“I’ve done every single job you have asked.”

“And what would you do if the job was to terminate Miss Vanya Hargreeves?”

***

Five could have killed the Handler immediately, but he took pleasure in her seeing how far she had failed before he did. 

He escaped the Commission quickly, landing in 2015 (he wanted to be there sooner than the time of the apocalypse, giving him plenty of room to work around, he would have to jump back further to save Ben once he was certain he could save him) in a body that was estimated to be about forty. He didn’t put much thought into it, going immediately to Vanya’s apartment.

When she opened the door, she was in a robe. He realized with guilt that she was waiting for him to watch her, but then he admonished himself for feeling that guilt. She actually had him now, and he could have her.

If she ever forgave him, that is.

“Vanya,” he breathed. She backed away a second, and he hastily showed her the tattoo on his hand. Her mouth opened to a little  _ o _ , and she traced the umbrella against his skin reverently. 

“ _ Five _ ,” she cried, already pulling him into a fierce hug. He stiffly stepped out of her embrace, and she looked him on in fear. 

“What is it?” she whispered. 

“Vanya, I watched you, on your cams,” he blurted. Goddammit, was he the actual idiot all along when he called everyone else that?

“You did?” she asked, not sounding judgemental.

“You’re not mad?”

“I hoped it was you,” she was already pulling him into another hug.

He was dazed. He had expected her to yell at him, to hate him. 

“Why are you not mad?” The astoundment was pretty clear in his voice. 

She dragged him to the couch he had seen in the videos. “You kept a roof over my head for one. Also, I always hoped it was you. When you didn’t give me your name, I kind of just let myself believe that it was you.”

“Which is why you said ‘Five’ that one time,” he noted. She blushed. It was cute. “You’re adorable.”

She giggled, trying to hide behind bangs that didn’t exist anymore. 

Five kissed her. 

“How do you feel about one more show?” He whispered into her ear. 

She laughed. “What do you have in mind?”

He fucked her with the webcam pointing at them. Her face was obscured, but he made sure he was staring directly into the camera at who he knew was watching as he barked out praise to Vanya and told her that she was the greatest thing to ever happen to him, that he loved her, that she was all he ever wanted. 

As he spilled inside of her, fingers one one hand tweaking at her nipples and the other fingers mercilessly circling against her clit, he hoped the message was clear. 

Five was loyal to Vanya only. 

**Author's Note:**

> Thank you all for reading!! This will not be extended and will remain a one-shot!!


End file.
